2-(7-chloro-1H-indol-3-yl)-2-oxoacetyl chloride | 863289-28-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-(7-chloro-1H-indol-3-yl)-2-oxoacetyl chloride
• CAS: 863289-28-5
• 化学式: C₁₀H₅Cl₂NO₂
• 分子量: 242.061
• InChiKey: VQFRPJBOAXPNCA-UHFFFAOYSA-N

物化性质

• 沸点：
  444.4±48.0 °C(Predicted)
• 密度：
  1.573±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(7-chloro-1H-indol-3-yl)-2-oxoacetyl chloride 在 lithium aluminium tetrahydride 、 氨 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 生成 2-(7-氯-1H-吲哚-3-基)乙胺
  参考文献：
  名称：

  固相合成N，N-二甲基色胺和β-咔啉的通用连接策略。

  摘要：

  乙烯基磺酰基甲基聚苯乙烯树脂可捕获各种色胺，从而产生安全连接。β-咔啉可通过引入R（1）的Pictet-Spengler反应由4形成。色胺4也可以通过酰化或铜介导的偶联引入R（2）衍生化。如果X = Br，则可以使用Suzuki耦合来引入R（3）。衍生化后，吲哚衍生物被甲基碘活化并在温和的碱性条件下释放。[反应：看文字]

  DOI：

  10.1021/ol026729p
• 作为产物：
  描述：

  7-氯吲哚 、 草酰氯 以 乙醚 为溶剂， 生成 2-(7-chloro-1H-indol-3-yl)-2-oxoacetyl chloride
  参考文献：
  名称：

  固相合成N，N-二甲基色胺和β-咔啉的通用连接策略。

  摘要：

  乙烯基磺酰基甲基聚苯乙烯树脂可捕获各种色胺，从而产生安全连接。β-咔啉可通过引入R（1）的Pictet-Spengler反应由4形成。色胺4也可以通过酰化或铜介导的偶联引入R（2）衍生化。如果X = Br，则可以使用Suzuki耦合来引入R（3）。衍生化后，吲哚衍生物被甲基碘活化并在温和的碱性条件下释放。[反应：看文字]

  DOI：

  10.1021/ol026729p

文献信息

• A Versatile Linkage Strategy for Solid-Phase Synthesis of <i>N</i>,<i>N</i>-Dimethyltryptamines and β-Carbolines
  作者：Tom Y. H. Wu、Peter G. Schultz

  DOI：10.1021/ol026729p

  日期：2002.11.1

  Various tryptamines are captured by a vinylsulfonylmethyl polystyrene resin, generating a safety-catch linkage. Beta-carbolines can be formed from 4 by a Pictet-Spengler reaction with the introduction of R(1). Tryptamine 4 can also be derivatized by acylation or copper-mediated coupling to introduce R(2). If X = Br, Suzuki coupling can be used to introduce R(3). After derivatization, the indole derivatives

  乙烯基磺酰基甲基聚苯乙烯树脂可捕获各种色胺，从而产生安全连接。β-咔啉可通过引入R（1）的Pictet-Spengler反应由4形成。色胺4也可以通过酰化或铜介导的偶联引入R（2）衍生化。如果X = Br，则可以使用Suzuki耦合来引入R（3）。衍生化后，吲哚衍生物被甲基碘活化并在温和的碱性条件下释放。[反应：看文字]
• 3-Thio-1,2,4-triazoles, novel somatostatin sst2/sst5 agonists
  作者：Marie-Odile Contour-Galcéra、Alban Sidhu、Pascale Plas、Pierre Roubert

  DOI：10.1016/j.bmcl.2005.05.061

  日期：2005.8

  Novel 3-thio-1,2,4-triazoles have been obtained via a solution-phase parallel synthesis strategy, affording potent non-peptidic human somatostatin receptor subtypes 2 and 5 agonists. (c) 2005 Elsevier Ltd. All rights reserved.
• A new synthesis of versatile indolyl-3-carbonylnitriles
  作者：Clinton G.L. Veale

  DOI：10.1016/j.tetlet.2015.07.075

  日期：2015.9

  Indolyl-3-carbonylnitriles are compounds with demonstrated utility as intermediates in organic chemistry. However, their synthesis remains a challenge, requiring the use of toxic sources Of cyanide, and often proceeding in low yields. Accordingly, presented here is a new synthesis of these versatile reactants, via dehydration of easily accessible alpha-oxoacetamides in generally high yields under simple reaction conditions. (C) 2015 Elsevier Ltd. All rights reserved.
• Exploration of the antibiotic potentiating activity of indolglyoxylpolyamines
  作者：Melissa M. Cadelis、Elliot I.W. Pike、Weirong Kang、Zimei Wu、Marie-Lise Bourguet-Kondracki、Marine Blanchet、Nicolas Vidal、Jean Michel Brunel、Brent R. Copp

  DOI：10.1016/j.ejmech.2019.111708

  日期：2019.12

  A series of substituted di-indolglyoxylamido-spermine analogues were prepared and evaluated for intrinsic antimicrobial properties and the ability to enhance antibiotic action. As a compound class, intrinsic activity was typically observed towards Gram-positive bacteria and the fungus Cryptococcus neoformans, with notable exceptions being the 5-bromo- and 6-chloro-indole analogues which also exhibited modest activity (MIC 34-50 mu M) towards the Gram-negative bacteria Escherichia coli and Klebsiella pneumoniae. Several analogues enhanced the activity of doxycycline towards the Gram-negative bacteria Pseudomonas aeruginosa, E. coli, K. pneumoniae and Acinetobacter baumannii. Of particular note was the identification of five antibiotic enhancing analogues (5-Br, 7-F, 5-Me, 7-Me, 7-Me) which also exhibited low to no cytotoxicity and red blood cell haemolytic properties. The mechanisms of action of the 5-Br and 7-F analogues were attributed to the ability to disrupt the integrity of, and depolarize, bacterial membranes. (C) 2019 Elsevier Masson SAS. All rights reserved.
• Alpha-ethyltryptamines as dual dopamine–serotonin releasers
  作者：Bruce E. Blough、Antonio Landavazo、John S. Partilla、Ann M. Decker、Kevin M. Page、Michael H. Baumann、Richard B. Rothman

  DOI：10.1016/j.bmcl.2014.07.062

  日期：2014.10

  The dopamine (DA), serotonin (5-HT), and norepinephrine (NE) transporter releasing activity and serotonin-2A (5-HT2A) receptor agonist activity of a series of substituted tryptamines are reported. Three compounds, 7b, (+)-7d and 7f, were found to be potent dual DA/5-HT releasers and were > 10-fold less potent as NE releasers. Additionally, these compounds had different activity profiles at the 5-HT2A receptor. The unique combination of dual DA/5-HT releasing activity and 5-HT2A receptor activity suggests that these compounds could represent a new class of neurotransmitter releasers with therapeutic potential. (C) 2014 Elsevier Ltd. All rights reserved.